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Our top choices for Chesapeake holiday rentals

1. Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Huntington
10.0 out of 10, Exceptional, (32 reviews)
"It was a great place to stay."
United States
Mary Susan A.
The price is £166
includes taxes & fees
2 Oct - 3 Oct
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

2. Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Great space for family gathering for our Marshall grad. Very cute, spacious and centrally located."
United States
Carrie S.
The price is £243
includes taxes & fees
27 Oct - 28 Oct
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

3. The Park House A 5 Bedroom Retreat w/Game Room &

The Park House A 5 Bedroom Retreat w/Game Room &
Huntington
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful place, loved the decor and home away from home."
United States
Yvette H.
The price is £564
includes taxes & fees
4 Oct - 5 Oct
The Park House A 5 Bedroom Retreat w/Game Room &

4. Huntington Modern History - 4BD, MU, DT, St Mary's

Huntington Modern History - 4BD, MU, DT, St Mary's
Huntington
10.0 out of 10, Exceptional, (13 reviews)
"It was a great, historic home. We loved how the owners have kept the original details and the space worked very well for a family of four. "
United States
Brian B.
The price is £550
includes taxes & fees
8 Oct - 9 Oct
Huntington Modern History - 4BD, MU, DT, St Mary's

5. 2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Kenova
10.0 out of 10, Exceptional, (60 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is £148
includes taxes & fees
5 Oct - 6 Oct
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

6. Espresso Maker & Modern Decor by Arena, University, Hospitals

Espresso Maker & Modern Decor by Arena, University, Hospitals
Huntington
10.0 out of 10, Exceptional, (3 reviews)
"The place was very cozy and had everything you would need for your stay"
United States
Kellie V.
The price is £240
includes taxes & fees
4 Oct - 5 Oct
Espresso Maker & Modern Decor by Arena, University, Hospitals

7. Charming Home with private Hot Tub and Fire Pit

Charming Home with private Hot Tub and Fire Pit
South Point
10.0 out of 10, Exceptional, (15 reviews)
"The cleanliness and the small special items example the bottle of wine and snacks if we wanted them. Will definitely stay here again if we travel that way. "
United States
Elizabeth C.
The price is £138
includes taxes & fees
8 Oct - 9 Oct
Charming Home with private Hot Tub and Fire Pit

8. Cozy With A Little Touch of Love

Cozy With A Little Touch of Love
Huntington
7.8 out of 10, Good, (6 reviews)
"Had a nice weekend stay here while in Huntington working. It was nice an quiet! Landlord was great!"
United States
Amanda P.
The price is £333
includes taxes & fees
10 Oct - 11 Oct
Cozy With A Little Touch of Love

9. Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Property was exactly as described. Wish we would have found it sooner. Will definitely be back. Nice cozy place and very affordable. "
United States
richie k.
The price is £262
includes taxes & fees
4 Oct - 5 Oct
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

10. Convenient 1-BR - Fenced Backyard - Extended Stays wanted

Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Huntington
8.0 out of 10, Very good, (1 review)
The price is £239
includes taxes & fees
5 Oct - 6 Oct
Convenient 1-BR - Fenced Backyard - Extended Stays wanted

11. The Chessie Room - Historic Boutique Stay at Heritage Station

The Chessie Room - Historic Boutique Stay at Heritage Station
Huntington
10.0 out of 10, Exceptional, (1 review)
The price is £146
includes taxes & fees
2 Oct - 3 Oct
The Chessie Room - Historic Boutique Stay at Heritage Station

12. Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Very nicely decorated, cozy and clean."
United States
Yvette H.
The price is £242
includes taxes & fees
6 Oct - 7 Oct
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

13. Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Huntington
The price is £1,152
includes taxes & fees
1 Nov - 2 Nov
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

14. Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Ashland
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stay. Very modern and comfortable. Philip is a nice guy to deal with."
United States
Paul M.
The price is £143
includes taxes & fees
5 Oct - 6 Oct
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

15. Cozy Fonzie Flat

Cozy Fonzie Flat
Ashland
10.0 out of 10, Exceptional, (1 review)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is £243
includes taxes & fees
2 Oct - 3 Oct
Cozy Fonzie Flat

16. THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (241 reviews)
"Host was great with communication, check in was a breeze and the property was beautiful. We caught about 30 fish in total between my husband and I. We will definitely be back!"
United States
Whitney M.
The price is £241
includes taxes & fees
4 Oct - 5 Oct
THE LUXURY CABIN IN THE WOODS

17. La'Chic Boutique Bungalow 3 Beds/1.5Baths

La'Chic Boutique Bungalow 3 Beds/1.5Baths
Ashland
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed all the comfort of home."
United States
scott j.
The price is £236
includes taxes & fees
23 Oct - 24 Oct
La'Chic Boutique Bungalow 3 Beds/1.5Baths

18. The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Catlettsburg
10.0 out of 10, Exceptional, (127 reviews)
"This was a great getaway with everything you could need great place for couples and family's."
United States
Andrew B.
The price is £167
includes taxes & fees
6 Oct - 7 Oct
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

19. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
9.0 out of 10, Wonderful, (7 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is £141
includes taxes & fees
11 Oct - 12 Oct
Charming 3BR Home - Near KDMC & Downtown

20. Spacious Historic 5-bedroom house in charming Barboursville with AC

Spacious Historic 5-bedroom house in charming Barboursville with AC
Barboursville
10.0 out of 10, Exceptional, (2 reviews)
"Very cozy and nice place!"
United States
Joseph S.
The price is £468
includes taxes & fees
6 Oct - 7 Oct
Spacious Historic 5-bedroom house in charming Barboursville with AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as £128 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ohio River Valley. In the wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.